1-cyclohexyl-3-(4-methoxyphenyl)-2-propyn-1-ol | 134260-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-cyclohexyl-3-(4-methoxyphenyl)-2-propyn-1-ol
• 英文别名: 1-cyclohexyl-3-(4-methoxyphenyl)prop-2-yn-1-ol
• CAS: 134260-68-7
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: RSZKKQHDQFRUNH-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±27.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-3-(4-methoxyphenyl)-2-propyn-1-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 苯酚 作用下， 以 二氯甲烷 、 邻二氯苯 为溶剂， 反应 26.0h， 生成 C₁₉H₂₀O₃
  参考文献：
  名称：

  合成方法塞科-tetracenomycin天然产品saccharothrixone A-C

  摘要：

  设计与第一合成方法来结构新颖的功能四环框架的发展塞科已经报道-tetracenomycin天然产物saccharothrixones A-C。芳烃-炔烃单元的热脱氢狄尔斯-阿尔德反应已被用作关键的合成步骤。这种策略已经被延长的多样功能四环系统的一个小型图书馆的产生塞科-tetracenomycins。还已经描述了合成多羟基四环系统的方法。本报告代表了土霉素的天然产物糖醋曲酮A–C的第一种合成方法。

  DOI：

  10.1016/j.tetlet.2018.04.031
• 作为产物：
  描述：

  (4-甲氧基苯乙炔基)三甲基硅烷 、 环己烷基甲醛 在 P(PhCH₂NCH₂CH₂)3N 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以92%的产率得到1-cyclohexyl-3-(4-methoxyphenyl)-2-propyn-1-ol
  参考文献：
  名称：

  P(PhCH₂NCH₂CH₂)₃N: An Efficient Lewis Base Catalyst for the Synthesis of Propargylic Alcohols and Morita−Baylis−Hillman Adducts via Aldehyde Alkynylation

  摘要：

  Proazaphosphatrane P(PhCH2NCH2CH2)(3)N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes in THF at room temperature. The reaction conditions are mild and employ a low catalyst loading (ca. 5 mol %). Only propargylic alcohols were isolated in good to excellent isolated yields when electron-rich, electron-neutral, heterocyclic, and aliphatic aldehydes were employed, whereas beta-branched Morita-Baylis-Hillman (MBH) type adducts were isolated with electron-deficient aromatic aldehydes after conventional acid hydrolysis of the TMS ether products. Alkynes containing heterocyclic and aromatic groups bearing electron-withdrawing or -donating substituents underwent clean addition to cyclohexanecarboxaldehyde and to electron-rich aromatic aldehydes to give propargylic alcohols in excellent isolated yields. beta-Branched Morita-Baylis-Hillman (MBH) type adducts were isolated when electron-deficient aromatic aldehydes were employed. Reaction pathways to both types of products are proposed.

  DOI：

  10.1021/jo9012332

文献信息

• Cooperative Catalysis of Metal and OH⋅⋅⋅O/sp³-CH⋅⋅⋅O Two-Point Hydrogen Bonds in Alcoholic Solvents: Cu-Catalyzed Enantioselective Direct Alkynylation of Aldehydes with Terminal Alkynes
  作者：Takaoki Ishii、Ryo Watanabe、Toshimitsu Moriya、Hirohisa Ohmiya、Seiji Mori、Masaya Sawamura

  DOI：10.1002/chem.201301280

  日期：2013.9.27

  with a transition‐metal center in alcoholic solvents for enantioselective catalysis. Copper(I) complexes with prolinol‐based hydroxy amino phosphane chiral ligands catalytically promoted the direct alkynylation of aldehydes with terminal alkynes in alcoholic solvents to afford nonracemic secondary propargylic alcohols with high enantioselectivities. Quantum‐mechanical calculations of enantiodiscriminating

  与酶催化相反，人造催化剂中的催化剂-底物氢键通常发生在质子惰性溶剂中，而不是质子溶剂中。我们报道了一种情况，其中配体与底物的氢键相互作用与含酒精溶剂中的过渡金属中心协同进行对映选择性催化。在醇溶剂中，具有脯氨醇基羟基氨基膦手性配体的铜（I）配合物催化促进醛与末端炔的直接烷基化，从而提供具有高对映选择性的非外消旋仲炔丙醇。enantiodiscriminating过渡态的量子力学的计算表明一个非经典SP的发生3 -C H⋅⋅⋅O氢键是配体与底物之间的次要相互作用，这导致了催化剂-底物的高方向性两点氢键。
• Dual Catalysis with Copper and Rhenium for Trifluoromethylation of Propargylic Alcohols: Efficient Synthesis of α-Trifluoromethylated Enones
  作者：Hiromichi Egami、Takafumi Ide、Masashi Fujita、Toshifumi Tojo、Yoshitaka Hamashima、Mikiko Sodeoka

  DOI：10.1002/chem.201403447

  日期：2014.9.15

  Trifluoromethylation of propargylic alcohols to provide (Z)‐α‐trifluoromethylated enones and β‐unsubstituted α‐trifluoromethylated enones proceeded with high yield and selectivity in the presence of CuI/Re2O7. The Z isomer was formed under kinetic control, though it is less stable than the E isomer in terms of steric repulsion.

  在CuI / Re 2 O 7存在下，炔丙醇进行三氟甲基化以提供（Z）-α-三氟甲基化的烯酮和β-未取代的α-三氟甲基化的烯酮。该ž异构体动力学控制下形成的，虽然它比少稳定ê在空间排斥方面异构体。
• Tin ditriflate-promoted addition of 1-alkynes to aldehydes
  作者：Masahiko Yamaguchi、Akio Hayashi、Toru Minami

  DOI：10.1021/jo00013a003

  日期：1991.6

  1-Alkynes add to aldehydes and ketones in the presence of Sn(OTf)2 and an amine giving acetylenic alcohols in high yields.
• YAMAGUCHI, MASAHIKO;HAYASHI, AKIO;MINAMI, TORU, J. ORG. CHEM., 56,(1991) N3, C. 4091-4092
  作者：YAMAGUCHI, MASAHIKO、HAYASHI, AKIO、MINAMI, TORU

  DOI：——

  日期：——